glycopyrrolate   

GtoPdb Ligand ID: 7459

Synonyms: AHR-504 | Qbrexza® (glycopyrronium cloth) | Robinul® | Seebri Neohaler® | Tovanor Breezhaler®
glycopyrrolate is an approved drug (FDA (1961), EMA (2012))
Compound class: Synthetic organic
Comment: Glycopyrrolate is the active moiety of the approved drug glycopyrronium bromide. It is an anticholinergic drug.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 46.53
Molecular weight 318.21
XLogP 2.59
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C(C(c1ccccc1)(C1CCCC1)O)OC1CC[N+](C1)(C)C
Isomeric SMILES O=C(C(c1ccccc1)(C1CCCC1)O)OC1CC[N+](C1)(C)C
InChI InChI=1S/C19H28NO3/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3/q+1
InChI Key ANGKOCUUWGHLCE-UHFFFAOYSA-N
References
1. Hansel TT, Neighbour H, Erin EM, Tan AJ, Tennant RC, Maus JG, Barnes PJ. (2005)
Glycopyrrolate causes prolonged bronchoprotection and bronchodilatation in patients with asthma.
Chest, 128 (4): 1974-9. [PMID:16236844]
2. Stocks MJ, Alcaraz L, Bailey A, Bowers K, Donald D, Edwards H, Hunt F, Kindon N, Pairaudeau G, Theaker J et al.. (2010)
The discovery of new spirocyclic muscarinic M3 antagonists.
Bioorg. Med. Chem. Lett., 20 (24): 7458-61. [PMID:21036043]
3. Tzelepis G, Komanapolli S, Tyler D, Vega D, Fulambarker A. (1996)
Comparison of nebulized glycopyrrolate and metaproterenol in chronic obstructive pulmonary disease.
Eur. Respir. J., 9 (1): 100-3. [PMID:8834341]